The suede knee-high with a stacked heel (left) is the Birkin bag of boots: object of desire, trend-defying classic, future icon (Hermès, $2,250). Think ten, 20, even 30 years ahead, and the initial outlay may not seem so outrageous. Coat, Sportmax.

The Height of Fashion:Over-the-knee boots (right) are leading the pack this season (Devani, $165). They camouflage all manner of leg issues (knobby knees, bigger thighs), can be worn full-length or folded down, and look fantastic over leggings or under skirts. Both pairs shown here are in the latest go-with-everything neutrals—beigy grays that you might call (with apologies to the bearded collies) Weimaraner colors. Jacket, 'S by Max Mara. Leggings, Tse.